Page last updated: 2024-11-05

2-methyl-1,4-benzoquinone

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

2-Methyl-1,4-benzoquinone, also known as toluquinone, is a naturally occurring quinone found in various plants and fungi. It exhibits a wide range of biological activities, including antioxidant, anti-inflammatory, and antimicrobial properties. It is synthesized through various methods, including oxidation of 2-methylphenol (o-cresol) or via enzymatic reactions in plants. Its importance lies in its potential therapeutic applications in treating conditions like inflammation, cancer, and infections. Research on 2-methyl-1,4-benzoquinone focuses on its mechanisms of action, its role in plant defense, and its potential as a lead compound for drug development.'

cresoquinone: no further information available 6/2003 [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID11122
CHEMBL ID358225
SCHEMBL ID49207
MeSH IDM0126433

Synonyms (71)

Synonym
hsdb 5495
ccris 7148
toluquinone (van)
2-methyl-1,4-benzochinon [czech]
1,4-toluchinon [czech]
1,4-benzoquinone, 2-methyl-
einecs 209-056-2
nsc 405002
ai3-14931
para-toluquinone
2-methyl-2,5-cyclohexadiene-1,4-dione
inchi=1/c7h6o2/c1-5-4-6(8)2-3-7(5)9/h2-4h,1h
2,5-cyclohexadiene-1,4-dione, 2-methyl-
2-methylbenzo-1,4-quinone
nsc405002
nsc-405002
2-methylquinone
nsc-1
wln: l6v dvj b1
2-methyl-1,4-benzoquinone
nsc1
toluquinone
1,4-toluquinone
553-97-9
2-methyl-1,4-quinone
p-benzoquinone, 2-methyl-
methyl-p-benzoquinone
methyl-1,4-benzoquinone
2,4-dione, 2-methyl-
methylquinone
2-methylbenzoquinone-1,4
2-methyl-p-benzoquinone
p-toluquinone
tolylquinone
methylbenzoquinone
2-methylbenzoquinone
methyl-p-benzoquinone, 98%
bdbm24780
2-methylcyclohexa-2,5-diene-1,4-dione
2-methyl-1,4-benzoquinone, 9
STK006340
CHEMBL358225
2-methyl-[1,4]benzoquinone
AKOS000492981
FT-0652794
M0159
methyl-p-quinone
T1244
A830622
1,4-toluchinon
vf06hb6azn ,
2-methyl-1,4-benzochinon
unii-vf06hb6azn
methyl quinone
2-methyl-1,4-benzoquinone [hsdb]
SCHEMBL49207
2-methyl benzoquinone
DTXSID8060290
W-105565
2-methylbenzo-1,4-quinone #
mfcd00001603
methyl-p-benzoquinone, 99%
toluchinon
AS-15293
BBL037012
Q27291795
2-methyl-p-quinone
CS-W011196
EN300-18167
Z57248271
cresoquinone
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Dihydroorotate dehydrogenase Schistosoma mansoniIC50 (µMol)57.00000.01901.94088.8000AID1592257
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (29)

Assay IDTitleYearJournalArticle
AID338273Toxicity against Artemia salina after 24 hrs1994Journal of natural products, Dec, Volume: 57, Issue:12
Biological effects of prenylated hydroquinones: structure-activity relationship studies in antimicrobial, brine shrimp, and fish lethality assays.
AID19832Partition coefficient (logP)1996Journal of medicinal chemistry, Feb-02, Volume: 39, Issue:3
In vivo activity and hydrophobicity of cytostatic aziridinyl quinones.
AID1592258Inhibition of human DHODH using DHO as substrate measured at 4 secs interval for 60 secs by DCIP reduction based indirect assay2019European journal of medicinal chemistry, Apr-01, Volume: 167Ligand-based design, synthesis and biochemical evaluation of potent and selective inhibitors of Schistosoma mansoni dihydroorotate dehydrogenase.
AID338270Antimicrobial activity against Candida albicans DSM 1665 after 18 hrs by twofold serial dilution method1994Journal of natural products, Dec, Volume: 57, Issue:12
Biological effects of prenylated hydroquinones: structure-activity relationship studies in antimicrobial, brine shrimp, and fish lethality assays.
AID19426HPLC capacity factor (logK)1996Journal of medicinal chemistry, Feb-02, Volume: 39, Issue:3
In vivo activity and hydrophobicity of cytostatic aziridinyl quinones.
AID1374919Growth inhibition of human OVCAR8 cells after 72 hrs by SRB assay2018Bioorganic & medicinal chemistry letters, 04-15, Volume: 28, Issue:7
The synthesis and evaluation of thymoquinone analogues as anti-ovarian cancer and antimalarial agents.
AID338268Antimicrobial activity against Bacillus subtilis DSM 347 after 18 hrs by twofold serial dilution method1994Journal of natural products, Dec, Volume: 57, Issue:12
Biological effects of prenylated hydroquinones: structure-activity relationship studies in antimicrobial, brine shrimp, and fish lethality assays.
AID1374920Growth inhibition of human A2780cis cells after 72 hrs by SRB assay2018Bioorganic & medicinal chemistry letters, 04-15, Volume: 28, Issue:7
The synthesis and evaluation of thymoquinone analogues as anti-ovarian cancer and antimalarial agents.
AID1374918Growth inhibition of human A2780 cells after 72 hrs by SRB assay2018Bioorganic & medicinal chemistry letters, 04-15, Volume: 28, Issue:7
The synthesis and evaluation of thymoquinone analogues as anti-ovarian cancer and antimalarial agents.
AID1091096Termiticidal activity against Coptotermes formosanus placed on 1 % wt/wt compound treated filter paper assessed as termite mortality measured 3 days post compound exposure2008Journal of agricultural and food chemistry, Jun-11, Volume: 56, Issue:11
Activity of 1,4-benzoquinones against formosan subterranean termites (Coptotermes formosanus).
AID326467Inhibition of purified human recombinant IDO2008Journal of medicinal chemistry, Mar-27, Volume: 51, Issue:6
Indoleamine 2,3-dioxygenase is the anticancer target for a novel series of potent naphthoquinone-based inhibitors.
AID338269Antimicrobial activity against Micrococcus luteus DSM 348 after 18 hrs by twofold serial dilution method1994Journal of natural products, Dec, Volume: 57, Issue:12
Biological effects of prenylated hydroquinones: structure-activity relationship studies in antimicrobial, brine shrimp, and fish lethality assays.
AID1592257Inhibition of Schistosoma mansoni DHODH using DHO as substrate measured at 4 secs interval for 60 secs by DCIP reduction based indirect assay2019European journal of medicinal chemistry, Apr-01, Volume: 167Ligand-based design, synthesis and biochemical evaluation of potent and selective inhibitors of Schistosoma mansoni dihydroorotate dehydrogenase.
AID224600Efficiency at pBR322 DNA interstand cross-linking at 10 uM1996Journal of medicinal chemistry, Jan-19, Volume: 39, Issue:2
Cross-linking and sequence specific alkylation of DNA BY aziridinylquinones. 1. Quinone methides.
AID224601Efficiency at pBR322 DNA interstand cross-linking at 100 uM1996Journal of medicinal chemistry, Jan-19, Volume: 39, Issue:2
Cross-linking and sequence specific alkylation of DNA BY aziridinylquinones. 1. Quinone methides.
AID338274Toxicity against Gambusia affinis1994Journal of natural products, Dec, Volume: 57, Issue:12
Biological effects of prenylated hydroquinones: structure-activity relationship studies in antimicrobial, brine shrimp, and fish lethality assays.
AID1374921Selectivity index, ratio of IC50 for SV-40 immortalized human ovarian epithelial cells to IC50 for human A2780cis cells2018Bioorganic & medicinal chemistry letters, 04-15, Volume: 28, Issue:7
The synthesis and evaluation of thymoquinone analogues as anti-ovarian cancer and antimalarial agents.
AID1181944Glutathione reactivity at 1 mM in presence of 1 mM glutathione containing PBS and 1 mM EDTA buffer at pH 7.4 assessed as remaining GSH level after 30 mins by spectrophotometry by Ellman's method2014Bioorganic & medicinal chemistry, Aug-01, Volume: 22, Issue:15
Benzoquinones as inhibitors of botulinum neurotoxin serotype A.
AID19838Partition coefficient (logP)1996Journal of medicinal chemistry, Feb-02, Volume: 39, Issue:3
In vivo activity and hydrophobicity of cytostatic aziridinyl quinones.
AID1091094Termiticidal activity against Coptotermes formosanus placed on 1 % wt/wt compound treated filter paper assessed as termite mortality measured 21 days post compound exposure2008Journal of agricultural and food chemistry, Jun-11, Volume: 56, Issue:11
Activity of 1,4-benzoquinones against formosan subterranean termites (Coptotermes formosanus).
AID338271Antimicrobial activity against Escherichia coli DSM 1103 after 18 hrs by twofold serial dilution method1994Journal of natural products, Dec, Volume: 57, Issue:12
Biological effects of prenylated hydroquinones: structure-activity relationship studies in antimicrobial, brine shrimp, and fish lethality assays.
AID338272Antimicrobial activity against Pseudomonas aeruginosa DSM 1117 after 18 hrs by twofold serial dilution method1994Journal of natural products, Dec, Volume: 57, Issue:12
Biological effects of prenylated hydroquinones: structure-activity relationship studies in antimicrobial, brine shrimp, and fish lethality assays.
AID1181943Glutathione reactivity at 1 mM in presence of 1 mM glutathione containing PBS and 1 mM EDTA buffer at pH 7.4 assessed as remaining GSH level after 10 seconds by spectrophotometry by Ellman's method2014Bioorganic & medicinal chemistry, Aug-01, Volume: 22, Issue:15
Benzoquinones as inhibitors of botulinum neurotoxin serotype A.
AID96156In vitro cytotoxicity against Human Chronic Leukemia K562 cells1996Journal of medicinal chemistry, Jan-19, Volume: 39, Issue:2
Cross-linking and sequence specific alkylation of DNA BY aziridinylquinones. 1. Quinone methides.
AID1592252Inhibition of Schistosoma mansoni DHODH assessed as remaining enzyme activity at 500 uM using DHO as substrate measured at 4 secs interval for 60 secs by DCIP reduction based indirect assay relative to control2019European journal of medicinal chemistry, Apr-01, Volume: 167Ligand-based design, synthesis and biochemical evaluation of potent and selective inhibitors of Schistosoma mansoni dihydroorotate dehydrogenase.
AID1181939Inhibition of recombinant Clostridium botulinum neurotoxin serotype A light chain assessed as Kinact to KI ratio at 50 uM after 1.5 hrs by SNAPtide FRET based assay2014Bioorganic & medicinal chemistry, Aug-01, Volume: 22, Issue:15
Benzoquinones as inhibitors of botulinum neurotoxin serotype A.
AID1374928Growth inhibition of SV-40 immortalized human ovarian epithelial cells after 72 hrs by SRB assay2018Bioorganic & medicinal chemistry letters, 04-15, Volume: 28, Issue:7
The synthesis and evaluation of thymoquinone analogues as anti-ovarian cancer and antimalarial agents.
AID1091127Antifeedant activity against Coptotermes formosanus placed on 1 % wt/wt compound treated filter paper assessed as filter paper consumption measured 21 days post compound exposure (Rvb = 85 +/- 15.1 mg)2008Journal of agricultural and food chemistry, Jun-11, Volume: 56, Issue:11
Activity of 1,4-benzoquinones against formosan subterranean termites (Coptotermes formosanus).
AID1091095Termiticidal activity against Coptotermes formosanus placed on 1 % wt/wt compound treated filter paper assessed as termite mortality measured 11 days post compound exposure2008Journal of agricultural and food chemistry, Jun-11, Volume: 56, Issue:11
Activity of 1,4-benzoquinones against formosan subterranean termites (Coptotermes formosanus).
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (27)

TimeframeStudies, This Drug (%)All Drugs %
pre-19903 (11.11)18.7374
1990's6 (22.22)18.2507
2000's9 (33.33)29.6817
2010's7 (25.93)24.3611
2020's2 (7.41)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 26.98

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index26.98 (24.57)
Research Supply Index3.40 (2.92)
Research Growth Index4.77 (4.65)
Search Engine Demand Index24.28 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (26.98)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies1 (3.45%)4.05%
Observational0 (0.00%)0.25%
Other28 (96.55%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]